The observation, Grignard reaction of cyclohexanone with tert -butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D 3 O + is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained. Concept introduction: Grignard reagents add to the carbonyl group in aldehydes and ketones . The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones. Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers. To explain: The observation, Grignard reaction of cyclohexanone with tert -butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D 3 O + is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

Question

Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

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Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.

Which of the following is the product in this Grignard reaction? ОН O 1) O 2) ОН 4) H.

What would be a proposed mechanism to get from cyclohexanol to cis-2-methoxycyclohexanol? I know how to get from cyclohexanol to trans-2-methoxycyclohexanol would be to go through acid-catalyzed dehydration via H2SO4, then epoxide ring formation via mCPBA and then alcohol-catalyzed opening, but don't know how to do for the cis version, if possible.

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

Expert Solution & Answer

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See solution

Check out sample textbook solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.SE, Problem 61AP

Interpretation Introduction